This small group discussion guide draws directly from the sermon “Showcase - Sunday Morning Worship Service 10:45am” so you can keep engaging with the message all week. Read, reflect, and share it with your small group or friends.

Small Group Discussion Guide

"Shrewd for Eternity: Using What Won't Last for What Will"

Based on Luke 16:1-9 | The Parable of the Shrewd Manager

"He is no fool who gives what he cannot keep to gain what he cannot lose." — Jim Elliott, missionary martyr (1956)

OVERVIEW

In this sermon, Pastor Ben Wales walks us through one of Jesus's most puzzling parables — the story of a dishonest manager who, facing termination, shrewdly uses his remaining time and resources to secure his future. Rather than commending dishonesty, Jesus uses this story to challenge his followers with a penetrating question: If worldly people are this strategic about their temporary futures, how much more should God's people be strategic about eternity? The central call of the message is this: Be shrewd with what is temporal to gain eternal reward — using our time, money, relationships, and influence not for fleeting comfort, but for lasting, kingdom impact.

BEFORE YOU MEET: A NOTE FOR FACILITATORS

Welcome! Whether this is your first time leading a small group or your fiftieth, this guide is designed to help you. You don't need to be a biblical scholar — your job is simply to create space for honest conversation and to help your group connect Sunday's message to Monday's life.

A few things to keep in mind:

You don't have to cover every question. Choose what fits your group best.
Silence is okay. Give people time to think before moving on.
Your own honest sharing will give others permission to share honestly too.
Aim for conversation, not a lecture. The best groups talk with each other, not just to each other.
Estimated total time: 75–90 minutes

SECTION 1: ICEBREAKER

⏱ Estimated Time: 5–10 minutes

Start here to warm up the group and get everyone talking before diving into deeper content.

Opening Question:

"Think about a time when you made a really smart, strategic decision — big or small — that paid off in the long run. What was the situation, and what made your decision a 'shrewd' one?"

(Examples might range from a financial investment to choosing a college, switching careers, or even picking the right checkout line at the grocery store! Keep it light and fun.)

[Leader Tip] This question is intentionally low-stakes and fun. Let it breathe. Laughter and lightness at the start help people relax and open up for deeper questions later. If your group is quiet, share your own example first to model vulnerability and set the tone.

SECTION 2: SCRIPTURE READING

⏱ Estimated Time: 5 minutes

Have someone read the passage aloud before discussion begins. You may want to invite two different people to read — one for the parable itself and one for Jesus's teaching that follows.

The Key Passage: Luke 16:1-9 (English Standard Version)

"He also said to the disciples, 'There was a rich man who had a manager, and charges were brought to him that this man was wasting his possessions. And he called him and said to him, "What is this that I hear about you? Turn in the account of your management, for you can no longer be manager." And the manager said to himself, "What shall I do, since my master is taking the management away from me? I am not strong enough to dig, and I am ashamed to beg. I have decided what to do, so that when I am removed from management, people may receive me into their houses." So, summoning his master's debtors one by one, he said to the first, "How much do you owe my master?" He said, "A hundred measures of oil." He said to him, "Take your bill, and sit down quickly and write fifty." Then he said to another, "And how much do you owe?" He said, "A hundred measures of wheat." He said to him, "Take your bill, and write eighty." The master commended the dishonest manager for his shrewdness. For the sons of this world are more shrewd in dealing with their own generation than the sons of light. And I tell you, make friends for yourselves by means of unrighteous wealth, so that when it fails, they may receive you into the eternal dwellings."'

Supporting Passages Referenced in the Sermon

On God's ownership of everything:

"Behold, to the LORD your God belong heaven and the heaven of heavens, the earth with all that is in it." — Deuteronomy 10:14

"The earth is the LORD's and the fullness thereof, the world and those who dwell therein." — Psalm 24:1

On stewardship and accountability:

"You are not your own, for you were bought with a price. So glorify God in your body." — 1 Corinthians 6:19b-20

On earthly vs. heavenly treasure:

"Do not lay up for yourselves treasures on earth, where moth and rust destroy and where thieves break in and steal, but lay up for yourselves treasures in heaven, where neither moth nor rust destroys and where thieves do not break in and steal. For where your treasure is, there your heart will be also." — Matthew 6:19-21

SECTION 3: DISCUSSION QUESTIONS

⏱ Estimated Time: 35–45 minutes

Work through these questions as a group. You don't need to cover all of them — choose 5–7 that feel most relevant to your group. Questions are organized from lighter and observational to deeper and more personal.

PART A: Understanding the Parable

Starting with what the text actually says

Question 1 — Observational

"Before Sunday's sermon, what was your first impression of this parable? Did it confuse you, bother you, or make sense? How did the sermon change or deepen your understanding of what Jesus was actually teaching?"

[Leader Tip] This is a great first question because it normalizes confusion — this parable genuinely puzzles people, and admitting that creates an honest starting point. There are no wrong answers here. The goal is simply to surface where people are coming from before going deeper.

Question 2 — Interpretive

"Pastor Ben pointed out that the master commended the manager not for his dishonesty, but for his shrewdness. In your own words, what does it mean to be 'shrewd'? Why do you think Jesus would hold up a flawed, self-serving character as an example for his followers?"

(Pastor Ben defined shrewdness as "having a sense for how things work, and then making choices so that they work out best for you in the long term.")

Question 3 — Interpretive

"Jesus says in verse 8 that 'the sons of this world are more shrewd in dealing with their own generation than the sons of light.' What do you think he means by that? Can you think of any examples — from your own life or from the world around you — where you've seen worldly people being more strategic about their futures than Christians are about eternity?"

[Leader Tip] John Calvin's quote from the sermon is helpful here if discussion stalls: "Heathen and worldly men are more industrious and clever in taking care of the ways and means of this fleeting world than God's children are in caring for the heavenly eternal life." You might read it aloud and ask, "Does this ring true to you? Why or why not?" Be careful not to let this become a session of criticizing non-Christians — the point is self-examination for the group.

PART B: The Three Principles

Going deeper into the sermon's main teaching points

Question 4 — Reflective

"Pastor Ben said that everything we have — our time, money, relationships, body, mind, and affections — belongs to God, not to us. How does it actually feel to hear that? Is that truth freeing, convicting, or uncomfortable — and why?"

(Deuteronomy 10:14 and Psalm 24:1 remind us that God owns everything. 1 Corinthians 6:19-20 says we are not even our own — we were bought with a price.)

Question 5 — Personal

"The sermon warned against two specific ways we waste the Master's possessions: wasting life on entertainment and wasting life pursuing riches. Which of those two temptations resonates more with you personally — and why? What does that 'waste' actually look like in your day-to-day life?"

[Leader Tip] This question invites genuine vulnerability. Model honesty yourself if you're the facilitator. Remind the group that this is a grace-filled space — the goal isn't shame, but honest reflection that leads to growth. If the group is hesitant, you might reframe: "Which of these do you think our culture struggles with more?" before making it personal.

Question 6 — Theological

"Pastor Ben contrasted 'unrighteous wealth' (earthly money and possessions) with 'true riches' (eternal reward). He said our earthly bank accounts are 'funny money' in God's eternal economy — but that we can use them to 'be rich toward God.' What do you think it looks like practically to use temporary things to gain eternal reward? What's an example from your own life or from someone you admire?"

(See Luke 16:11 and Matthew 6:19-21 for biblical context.)

Question 7 — Community

"Jesus's command in verse 9 is to 'make friends by means of unrighteous wealth' — using what we have to connect people to God and to each other. Pastor Ben applied this in two directions: making friends in the church and making friends in the world. Which of those two feels more natural to you, and which feels more challenging? Why?"

Question 8 — Inspiring

"Pastor Ben told the story of Jim Elliott, the missionary who was killed in Ecuador in 1956, and his famous journal entry: 'He is no fool who gives what he cannot keep to gain what he cannot lose.' Jim also wrote Luke 16:9 beneath that quote. What does it say about Jim Elliott's perspective on life that he was willing to give up everything — including his safety — for the sake of eternal friendship-making? How does his story challenge or inspire you?"

[Leader Tip] This question often generates powerful conversation, especially about sacrifice, calling, and what we're actually living for. Some group members may push back on Elliott's choices — welcome that honestly. The point isn't that everyone must be a missionary, but that everyone is called to live with an eternal perspective. You might follow up with: "You don't have to go to the jungle — but how is God calling you to live with that same kind of shrewdness right where you are?"

SECTION 4: PERSONAL APPLICATION

⏱ Estimated Time: 10–15 minutes

These questions are for more personal, individual reflection. You might invite people to take 2 minutes of quiet to think before sharing, or let people choose which question they want to respond to.

Application Question 1:

"The manager in the parable had a window of time — after his termination was announced but before he was escorted out — in which he still had authority and opportunity to act. Pastor Ben said: 'If we got up this morning, we still have a window of opportunity.' What does that window look like for you right now? What have you been putting off that you know God is calling you toward?"

Application Question 2:

"On a scale of 1 to 10, how 'shrewd' would you say you currently are with your time, money, and relationships when it comes to eternal priorities? What would it look like to move one number higher on that scale this week?"

Application Question 3:

"Pastor Ben mentioned several 'one another' commands from Scripture — serve one another, show hospitality to one another, encourage one another, walk in fellowship with one another. Is there a specific person in this group — or in your church community — that God might be nudging you to reach out to and invest in this week? What would that look like?"

Application Question 4:

"Think about someone in your life who is far from God. How might God be calling you to use what you have — your time, your home, your resources, your story — to 'make a friend' who might one day welcome you into eternal dwellings? What's one small, concrete step you could take toward that person this week?"

🎯 THIS WEEK'S CHALLENGE

Choose one of the following action steps before your group meets again:

Option	Action
Stewardship	Review one area of your finances and ask: "Am I using this to feather my earthly nest, or to invest in the eternal?" Make one intentional adjustment.
Community	Reach out to one person from church you don't know well. Invite them to coffee, send an encouraging text, or pray for them by name this week.
Friendship-Making	Identify one person in your life who is far from God. Do one thing this week to serve, listen to, or spend time with them — with no agenda other than love.
Reflection	Spend 15 minutes journaling on this question: "What am I holding onto that I cannot keep — and what would it look like to let it go for something eternal?"
Family/Household	Have one conversation with your spouse, child, or roommate about what it means to live with an eternal perspective. Share something from Sunday's message that challenged you.

SECTION 5: PRAYER FOCUS

⏱ Estimated Time: 5–10 minutes

Close your time together in prayer. You might invite several people to pray briefly, or have one person pray over the following themes. Feel free to adapt this to your group's culture and comfort level.

SECTION 6: OPTIONAL DEEP DIVE

⏱ For groups wanting to go further — or for a follow-up session

These questions are for groups with more time, more biblical background, or a desire to wrestle with the harder edges of the text.

Deep Dive Question 1 — Theological Tension

"This parable has puzzled Bible scholars for centuries. Some argue the manager was operating within his legitimate authority when he reduced the debts; others say he was being dishonest to the end. Does it change the meaning of the parable for you depending on which view is correct? Why or why not? What does Jesus's point remain regardless of the manager's specific method?"

(For further study: Compare this parable with the Parable of the Talents in Matthew 25:14-30 and the Parable of the Minas in Luke 19:11-27. What consistent teaching do you find about stewardship and accountability?)

Deep Dive Question 2 — The "How Much More" Argument

"Pastor Ben explained that Jesus often teaches from 'lesser to greater' — using flawed human examples to point to a much greater divine reality. He gave examples from the Parable of the Persistent Widow (Luke 18:1-8) and from Matthew 7:9-11. How does understanding this teaching method change the way you read and interpret difficult parables? Are there other places in Scripture where you've seen this pattern?"

Deep Dive Question 3 — Eternal Dwellings

"Jesus promises in verse 9 that when earthly wealth fails, friends will 'welcome you into eternal dwellings.' Pastor Ben said he doesn't know exactly what that means, but that it's 'eternal, unfaded, undefiled, and beyond what we can imagine.' What do you think this promise means? How does the hope of eternal community — with God and with the people we've loved and served — shape the way you want to live now? How does it compare to the way the world around you thinks about the future?"

(For further study: See 1 Peter 1:3-4, John 14:1-3, and Revelation 21:1-4 for other glimpses of the eternal home Jesus promises.)

SUPPLEMENTAL RESOURCES

For Further Reading & Listening:

Luke 16:10-18 — Read the rest of the chapter to see how Jesus extends his teaching on money, faithfulness, and God's enduring word
Luke 12:13-21 — The Parable of the Rich Fool (referenced in the sermon)
Luke 14:12-14 — Jesus's teaching on inviting the poor and marginalized to your table (referenced in the sermon)
Matthew 25:14-30 — The Parable of the Talents (a companion passage on faithful stewardship)
Randy Alcorn, Money, Possessions, and Eternity — A comprehensive biblical treatment of the themes in this sermon
Jim Elliot's biography: Shadow of the Almighty by Elisabeth Elliot

Key Quotes to Revisit:

"He is no fool who gives what he cannot keep to gain what he cannot lose." — Jim Elliott

"We are half-hearted creatures fooling about with drink and sex and ambition when infinite joy is offered us — like an ignorant child who wants to go on making mud pies in a slum because he cannot imagine what is meant by the offer of a holiday at the sea. We are far too easily pleased." — C.S. Lewis

"Heathen and worldly men are more industrious and clever in taking care of the ways and means of this fleeting world than God's children are in caring for the heavenly eternal life." — John Calvin

The Sermon's Three Main Principles — A Quick Reference:

Principle	Core Truth	Scripture
We are stewards of the Master	Everything belongs to God; we are accountable to him	Psalm 24:1; 1 Cor. 6:19-20
Earthly treasures are passing away	What we have on earth will fail; only the eternal lasts	Luke 16:11; Matt. 6:19-21
We are called to make friends	Use temporal resources to connect people to God and each other	Luke 16:9; Gal. 5:13

This guide was prepared for use in small groups at Shiloh Church. Feel free to adapt questions and timing to fit the needs of your specific group. May God use your time together to build his kingdom and deepen your community in Christ.

"And I tell you, make friends for yourselves by means of unrighteous wealth, so that when it fails, they may receive you into the eternal dwellings." — Luke 16:9

Showcase - Sunday Morning Worship Service 10:45am